When toluene reacts with chlorine in sunlight the first major product is__________________?
Correct answer: A. Benzy1 chloride
- A. Benzy1 chloride
- B. Benzal dichloride
- C. O-chlorotoluene
- D. O-chlorotoluene and P-chlorotoluene
Explanation
In sunlight, chlorine forms radicals and preferentially replaces a hydrogen at the benzylic position of toluene, producing benzyl chloride, C6H5CH2Cl. The benzylic radical is resonance-stabilised, so side-chain chlorination is favoured over ring substitution. Students may choose an o- or p-chlorotoluene by confusing photochemical radical substitution with electrophilic aromatic substitution.
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About Free Radical Substitution
Free radical substitution explains how alkanes react with halogens under ultraviolet light or heat through initiation, propagation and termination steps. The mechanism involves homolytic bond fission and radical intermediates, while product formation depends on the relative stability of radicals and differs from ionic substitution.
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